diff --git a/src/timetable_cmd.cpp b/src/timetable_cmd.cpp
index f68fabc366..29986c353d 100644
--- a/src/timetable_cmd.cpp
+++ b/src/timetable_cmd.cpp
@@ -384,6 +384,9 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 	if (v->current_order.IsType(OT_IMPLICIT)) return; // no timetabling of auto orders
 
+	if (v->cur_real_order_index >= v->GetNumOrders()) return;
+	Order *real_current_order = v->GetOrder(v->cur_real_order_index);
+
 	VehicleOrderID first_manual_order = 0;
 	for (Order *o = v->GetFirstOrder(); o != NULL && o->IsType(OT_IMPLICIT); o = o->next) {
 		++first_manual_order;
@@ -411,17 +414,20 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 	if (!HasBit(v->vehicle_flags, VF_TIMETABLE_STARTED)) return;
 
 	bool autofilling = HasBit(v->vehicle_flags, VF_AUTOFILL_TIMETABLE);
-	if (travelling && (!v->current_order.IsWaitTimetabled() ||
-			(autofilling && !HasBit(v->vehicle_flags, VF_AUTOFILL_PRES_WAIT_TIME)))) {
-		/* Need to clear that now as otherwise we are not able to reduce the wait time */
+	bool remeasure_wait_time = !real_current_order->IsWaitTimetabled() ||
+			(autofilling && !HasBit(v->vehicle_flags, VF_AUTOFILL_PRES_WAIT_TIME));
+
+	if (travelling && remeasure_wait_time) {
+		/* We just finished travelling and want to remeasure the loading time,
+		 * so do not apply any restrictions for the loading to finish. */
 		v->current_order.SetWaitTime(0);
 	}
 
 	if (just_started) return;
 
-	/* Modify station waiting time only if our new value is larger (this is
-	 * always the case when we cleared the timetable). */
-	if (!v->current_order.IsType(OT_CONDITIONAL) && (travelling || time_taken > v->current_order.GetWaitTime())) {
+	/* Before modifying waiting times, check whether we want to preserve bigger ones. */
+	if (!real_current_order->IsType(OT_CONDITIONAL) &&
+			(travelling || time_taken > real_current_order->GetWaitTime() || remeasure_wait_time)) {
 		/* Round the time taken up to the nearest day, as this will avoid
 		 * confusion for people who are timetabling in days, and can be
 		 * adjusted later by people who aren't.
@@ -433,9 +439,9 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 		 * processing of different orders when filling the timetable. */
 		uint time_to_set = CeilDiv(max(time_taken, 1U), DAY_TICKS) * DAY_TICKS;
 
-		if (travelling && (autofilling || !v->current_order.IsTravelTimetabled())) {
+		if (travelling && (autofilling || !real_current_order->IsTravelTimetabled())) {
 			ChangeTimetable(v, v->cur_real_order_index, time_to_set, MTF_TRAVEL_TIME, autofilling);
-		} else if (!travelling && (autofilling || !v->current_order.IsWaitTimetabled())) {
+		} else if (!travelling && (autofilling || !real_current_order->IsWaitTimetabled())) {
 			ChangeTimetable(v, v->cur_real_order_index, time_to_set, MTF_WAIT_TIME, autofilling);
 		}
 	}
@@ -450,8 +456,8 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 	if (autofilling) return;
 
-	uint timetabled = travelling ? v->current_order.GetTimetabledTravel() :
-			v->current_order.GetTimetabledWait();
+	uint timetabled = travelling ? real_current_order->GetTimetabledTravel() :
+			real_current_order->GetTimetabledWait();
 
 	/* Vehicles will wait at stations if they arrive early even if they are not
 	 * timetabled to wait there, so make sure the lateness counter is updated